NP-MRD: Showing NP-Card for [(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid (NP0270074)

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Record Information

Version

2.0

Created at

2022-09-08 15:45:49 UTC

Updated at

2022-09-08 15:45:49 UTC

NP-MRD ID

NP0270074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid

Description

Glucoisatisin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. [(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid is found in Isatis tinctoria. [(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid was first documented in 2008 (PMID: 18537074). Based on a literature review very few articles have been published on Glucoisatisin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217452D          

 37 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082217452D          

 37 39  0  0  1  0            999 V2000
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 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 28 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](S\C(C[C@@H](OC(=O)CC2C(O)=NC3=CC=CC=C23)C=C)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O12S2/c1-2-10(33-16(25)8-12-11-5-3-4-6-13(11)22-20(12)29)7-15(23-35-37(30,31)32)36-21-19(28)18(27)17(26)14(9-24)34-21/h2-6,10,12,14,17-19,21,24,26-28H,1,7-9H2,(H,22,29)(H,30,31,32)/b23-15-/t10-,12?,14+,17+,18-,19+,21-/m0/s1

> <INCHI_KEY>
NTDBYDWMVLRHLG-MTOHARGTSA-N

> <FORMULA>
C21H26N2O12S2

> <MOLECULAR_WEIGHT>
562.56

> <EXACT_MASS>
562.092716633

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.64034036441831

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(Z)-[(3R)-3-{[2-(2-hydroxy-3H-indol-3-yl)acetyl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxy}sulfonic acid

> <JCHEM_LOGP>
0.05707241702091264

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.361354455449883

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.420340854076204

> <JCHEM_PKA_STRONGEST_BASIC>
0.8333876759024514

> <JCHEM_POLAR_SURFACE_AREA>
224.99999999999994

> <JCHEM_REFRACTIVITY>
128.34830000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(Z)-[(3R)-3-{[2-(2-hydroxy-3H-indol-3-yl)acetyl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      13.059   0.721   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.725  -0.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.725  -1.589   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.392  -2.359   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.058  -1.589   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       7.724  -2.359   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       6.391  -1.589   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       5.057  -2.359   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0       4.287  -1.025   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.827  -3.692   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.723  -3.129   0.000  0.00  0.00           O+0
HETATM   12  S   UNK     0       9.058  -0.049   0.000  0.00  0.00           S+0
HETATM   13  C   UNK     0       7.724   0.721   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.391  -0.049   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.057   0.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.723  -0.049   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.390   0.721   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.057   2.261   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.723   3.031   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.391   3.031   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.391   4.571   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.724   2.261   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.058   3.031   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.059  -2.359   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.393  -1.589   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.393  -0.049   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.060  -1.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.221  -0.057   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.077   0.973   0.000  0.00  0.00           O+0
HETATM   31  N   UNK     0      18.727   0.263   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      19.497  -1.071   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      21.004  -1.391   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.480  -2.856   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.449  -4.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      18.943  -3.680   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.467  -2.215   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23                                                  
CONECT   23   22                                                            
CONECT   24    3   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32   28                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₁₂S₂

Average Mass

562.5600 Da

Monoisotopic Mass

562.09272 Da

IUPAC Name

{[(Z)-[(3R)-3-{[2-(2-hydroxy-3H-indol-3-yl)acetyl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxy}sulfonic acid

Traditional Name

[(Z)-[(3R)-3-{[2-(2-hydroxy-3H-indol-3-yl)acetyl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](S\C(C[C@@H](OC(=O)CC2C(O)=NC3=CC=CC=C23)C=C)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H26N2O12S2/c1-2-10(33-16(25)8-12-11-5-3-4-6-13(11)22-20(12)29)7-15(23-35-37(30,31)32)36-21-19(28)18(27)17(26)14(9-24)34-21/h2-6,10,12,14,17-19,21,24,26-28H,1,7-9H2,(H,22,29)(H,30,31,32)/b23-15-/t10-,12?,14+,17+,18-,19+,21-/m0/s1

InChI Key

NTDBYDWMVLRHLG-MTOHARGTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isatis tinctoria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
Indole or derivatives
Dihydroindole
Oxane
Benzenoid
Monothioacetal
Organic sulfuric acid or derivatives
Carboxamide group
Carboxylic acid ester
Lactam
Secondary alcohol
Secondary carboxylic acid amide
Sulfenyl compound
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Azacycle
Carboxylic acid derivative
Oxacycle
Alcohol
Organosulfur compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.057	ChemAxon
pKa (Strongest Acidic)	-2.4	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	225 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	128.35 m³·mol⁻¹	ChemAxon
Polarizability	51.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00026991

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101150466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mohn T, Hamburger M: Glucosinolate pattern in Isatis tinctoria and I. indigotica seeds. Planta Med. 2008 Jun;74(8):885-8. doi: 10.1055/s-2008-1074554. Epub 2008 Jun 6. [PubMed:18537074 ]
LOTUS database [Link]

Showing NP-Card for [(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid (NP0270074)

MOL for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

3D MOL for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

3D SDF for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

3D-SDF for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

PDB for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

3D PDB for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

SMILES for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

INCHI for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

Structure for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)

3D Structure for NP0270074 ([(z)-[(3r)-3-{[2-(2-hydroxy-3h-indol-3-yl)acetyl]oxy}-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene]amino]oxysulfonic acid)